Artist Isaac Pelayo Recalls Connecting With Westside Gunn & Selling A Biggie Painting To Diddy

There is more than one way to carve a legacy in the music industry; I was a music artist before ultimately carving out a career as an established writer. 24-year-old Visual Artist Isaac Pelayo is also in the same boat; he’s an active music artist and buzzing painter (an understatement as you’ll learn) who is making a mark as part of Westside Gunn’s historic run with his Griselda brand.

But, he’s been able to do so in the most unexpected way possible.

“I’ve been rapping since I was like 12, and I produce music as well, so I got into this culture in a way that I didn’t think I would,” he tells me via phone conversation on a warm summer night. 

Isaac has been the man responsible for such covers as the third eye Chris Benoit (used for his classic Supreme Blientele LP), the haunting Hitler Wears Hermes VI, Pray For Paris‘s alternate cover, and most recently, the cover of Armani Caesar’s debut, The Liz

He’s also been creating artwork for Gunn’s 4th Rope brand.

“Being able to create these album covers for Gunn and seeing how people associated it with the music … I’ve been lucky in this shit,” he says with a laugh.

The only thing more random and amazing than his current relationship with Griselda is the story of how it all came together.

“As an artist that doesn’t have a publicist, it’s tough to get write-ups and attention from publications,” he notes. “[Getting the story out] is crucial to me because that exposure is how people are going to get to know who I am, what I do and what my work is all about. 

“So, not having a publicist or someone to reach out publications for me, I took on that role myself.”

Artist Isaac Pelayo Recalls Connecting With Westside Gunn & Selling A Biggie Painting To Diddy

Isaac had done a few third eye images: notably, one of Tupac Shakur and one of Notorious B.I.G. — the latter is currently owned by Sean Combs (more on that later). After sending them to HipHopDX, the site posted his Tupac one, which led him to get noticed by Westside Gunn.

“[Gunn] hit me up in the DM,” he says. “He was like, ‘Bro; I fuck with your work … I’m trying to get some paintings from my crib. What do you got available? What’s your prices,’ all that stuff.

“So like a month later, he hit me up and was like, ‘You know what? I want you to do a painting for my album that I’m coming out with, Supreme Blientele.‘ It blew up from that fucking album!”

In many ways, Gunn and Isaac are quite similar in terms of their almost impulsive artistic inspiration. The story behind his alternate cover for Gunn’s Pray For Paris — the first time the rapper managed to impact the Billboard Hot 200 — is a great example.

“It was a situation where I got drunk one night on some depression during the fucking quarantine vibes … I was just alone in my studio pushing the paint,” he says. “It was the result of an angry, substance filled night. I was expressing what I was feeling at that moment, just, you know, this whole year just being crazy. 

“I texted Gunn, like, “Yo, this fucking quarantine got me painting a little differently … he was like, “Bro, I need that.” 

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At this point in our conversation, I felt compelled to come back to something crazy that Isaac had initially noted to me: Diddy owns a piece of his artwork.

I did that [Biggie] painting back in 2017 … I was living in Vegas at the time,” he says. “I got a homie who was close to Christian, Justin, and Quincy (Diddy’s sons). They are kind of like family through, you know, growing up around them in New York — they’re spitters too.”

After seeing his Tupac painting, the trio said if he were to make a Biggie one, they’d be able to get it to their father. “I ended up driving it from Vegas to Diddy’s spot in LA … dropped it off and was there for like 20 minutes in his doorway talking.

“It was crazy because Nipsey was working on Victory Lap, and the painting was in the background. Every time Nipsey is in the studio … It was kind of like an Easter egg. It was like the universe was saying, “Hey dog, your art is about to get plugged into some real Hip Hop shit. It wasn’t even my music that was like plugging me in. It was just my art, my first love; you know what I’m saying? I just wouldn’t have thought that.” 

The apple doesn’t fall far from the tree; Isaac’s father, Antonio Pelayo, is a celebrated artist. Aside from his artwork, Antonio produces popular events like La Bulla and El Velorio in L.A. (both of which celebrate Latinx music, food, art, wrestling and car cultures) — and Isaac regularly gets the opportunity to perform for crowds up to 6000+. 

Despite his father’s urging — and his evident love for his music — Isaac reveals to me he has yet to approach Gunn about it. He laughs as he realizes that he also hasn’t had the opportunity to tattoo him either. That’s yet another facet of his skillset. In fact, our interview ended as he was arriving at a client’s house for a private session. As of late, he’s be inking numerous mega-popular TikTok stars.

Admirably, he wants the discovery to feel organic and happen in its own time. Even without dropping bars, he still found himself aligned with Griselda’s storied rise.

“It’s a whole package. It’s not just one thing,” he explains, pointing to other supporting cast members like Daringer and Keisha Plum. “Everybody that’s in that vicinity, like, we’re all plugged into this little pocket of contribution. I’ve been insanely grateful to have contributed from a visual standpoint — and that it’s resonating with people.”

Follow Isaac on Instagram — and check out his latest single, “Bad Girl” below.

Riley About Author

Riley here — father, artist, videographer, professional writer and SERIOUS hip-hop head. I'm a member of the Universal Zulu Nation, and I think everything is better on vinyl. Add me on Twitter! @specialdesigns